diff --git a/addons/web_editor/static/src/js/editor/odoo-editor/src/commands/commands.js b/addons/web_editor/static/src/js/editor/odoo-editor/src/commands/commands.js
index 1f0fffc1814..e757deee2ee 100644
--- a/addons/web_editor/static/src/js/editor/odoo-editor/src/commands/commands.js
+++ b/addons/web_editor/static/src/js/editor/odoo-editor/src/commands/commands.js
@@ -377,7 +377,7 @@ export const editorCommands = {
         const changedElements = [];
         const defaultDirection = editor.options.direction;
         const shouldApplyStyle = !isSelectionFormat(editor.editable, 'switchDirection');
-        for (const block of new Set(selectedTextNodes.map(textNode => closestBlock(textNode)))) {
+        for (const block of new Set(selectedTextNodes.map(textNode => closestElement(textNode, 'ul,ol') || closestBlock(textNode)))) {
             if (!shouldApplyStyle) {
                 block.removeAttribute('dir');
             } else {
diff --git a/addons/web_editor/static/src/scss/web_editor.common.scss b/addons/web_editor/static/src/scss/web_editor.common.scss
index 3b523ccb920..b8c1ee47265 100644
--- a/addons/web_editor/static/src/scss/web_editor.common.scss
+++ b/addons/web_editor/static/src/scss/web_editor.common.scss
@@ -143,6 +143,7 @@ ul.o_checklist {
         list-style: none;
         position: relative;
         margin-left: $o-checklist-margin-left;
+        margin-right: $o-checklist-margin-left;
 
         &:not(.oe-nested)::before {
             content: '';
@@ -169,6 +170,11 @@ ul.o_checklist {
         }
     }
 }
+ul.o_checklist[dir="rtl"] > li:not(.oe-nested)::before {
+    left: auto;
+    right: - $o-checklist-margin-left;
+    text-align: right;
+}
 ol > li.o_indent, ul > li.o_indent {
     margin-left: 0;
     list-style: none;